2221+ Vacation Rentals Near Oregon Trail of Dreams |
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  2. Oregon
  3. Bend
  4. Oregon Trail of Dreams

Oregon Trail of Dreams All-Inclusive Resorts, Hotels & Rentals

Plan Your Next Vacation to Oregon Trail of Dreams to Relax, Recharge & Re-imagine

Property Image From $727
         

10.0 (145 Reviews)
House
The Executive Lodge up in the West Hills and is 2 miles from downtown Bend.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $241
         

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New
House
Aaron Way
  • Parking
  • Pet Friendly
  • Breakfast

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Property Image From $434
         

10.0 (71 Reviews)
House
351 m² House ∙ 5 bedrooms ∙ 14 guests
  • 3778 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $736
         

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10.0 (1 Review)
House
Vantage Point 3 Bedroom Townhouse by RedAwning
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

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Property Image From $739
         

9.8 (88 Reviews)
House
Gorgeous! Hot Tub, Mountain Views, Road to Mt Bachelor!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $267
         

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4.0 (2 Reviews)
House
Historic Farmhouse on Bends Westside
  • Parking
  • Balcony/Terrace
  • Child Friendly

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Property Image From $242
         

10.0 (49 Reviews)
House
186 m² House ∙ 3 bedrooms ∙ 7 guests
  • 2004 ft² House
  • Air Conditioner
  • Parking
  • TV

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Property Image From $79
         

8.4 (114 Reviews)
Hostel
Bunk+Brew Historic Lucas House - Hostel
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $237
         

9.8 (70 Reviews)
House
Great Reviews │West Side Bungalow │Walk Everywhere │Hot Tub │One Block to River
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $122
         

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10.0 (3 Reviews)
House
Lavender Hollow
  • Pet Friendly
  • Security/Safety
  • Sports/Activities

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Property Image From $325
         

10.0 (45 Reviews)
House
256 m² House ∙ 3 bedrooms ∙ 8 guests
  • 2755 ft² House
  • Air Conditioner
  • Parking
  • TV

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Property Image From $506
         

New
Apartment
Rooftop Deck Walk to River Downtown Fire pit
  • Sports/Activities
  • Entertainment
  • Barbecue/Outdoor Cooking

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Property Image From $385
         

9.8 (55 Reviews)
House
West Side Gem │Two King Suites │Walk Everywhere │Hot Tub │Large Living Space
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $112
         

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10.0 (3 Reviews)
House
Ponderosa Views
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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Property Image From $202
         

9.8 (51 Reviews)
Cottage
Contemporary Chic │West Side │Walk Everywhere │Hot Tub │One Block to River
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $271
         

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10.0 (2 Reviews)
House
Five Peaks
  • Parking
  • Pet Friendly
  • Security/Safety

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Property Image From $393
         

9.8 (111 Reviews)
House
Amazing! Steps to Downtown & River, Gorgeous, Newer, A/C
  • Air Conditioner
  • Parking
  • TV

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Property Image From $212
         

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10.0 (2 Reviews)
House
The Ark at Farewell Park, 20 Mi to Mt Bachelor!
  • Parking
  • View
  • Ocean View

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Property Image From $274
         

9.8 (88 Reviews)
House
Bend River Cottage – Pet-Friendly, Historic, Walkable to Old Mill & Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $2,368
         

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10.0 (1 Review)
House
Aerie Stylish 6 Unit Buyout 15BDR Near Downtown Mountain Views Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $591
         

9.6 (86 Reviews)
House
River Front on Mirror Pond & Drake Park, Exquisite, Gourmet Kitchen
  • Air Conditioner
  • Parking
  • TV

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Property Image From $986
         

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10.0 (1 Review)
House
Flagline Trail home
  • Air Conditioner
  • Parking
  • Security/Safety

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Property Image From $314
         

10.0 (90 Reviews)
House
Gorgeous and Updated! Perfect Location in NW Bend, Pool Table, 20 Min To Bachelor!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Property Image From $209
         

9.6 (168 Reviews)
Cottage
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries
  • Air Conditioner
  • Parking
  • Pet Friendly

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Weather in Oregon Trail of Dreams

View the weather forecast for Oregon Trail of Dreams before booking your Oregon Trail of Dreams Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Oregon Trail of Dreams, OR

Allinclusivebeachresorts offers a large selection of top attractions around Oregon Trail of Dreams. Research things to do on your vacation before you visit Oregon Trail of Dreams.


Old Mill District Les Schwab Amphitheater Deschutes Brewery Downtown Bend Business Association Drake Park Tower Theater Bend Rock Gym Deschutes National Forest Widgi Creek Golf Club Bend River Promenade Tetherow Golf Club Central Bend Sunriver Resort Golf Course Central Oregon Community College The Village High Desert Museum Cascade Range Sunriver Homeowners Aquatic & Recreation Center Bend Factory Stores Westside Church